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Volumn 76, Issue 2, 2011, Pages 557-565

Mercury(II)-mediated cleavage of cyclopropylcarbinols by an intramolecular sulfinyl group as a stereo-and regioselective route to stereotriads and stereotetrads

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOMERIC; REGIOSELECTIVE ROUTES; STEREOGENIC CENTERS; SULFINYL GROUP;

EID: 78651502125     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1019909     Document Type: Article
Times cited : (13)

References (72)
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    • For some applications of the ring-opening of cyclopropanes with mercury(II) salts, see
    • For some applications of the ring-opening of cyclopropanes with mercury(II) salts, see: Landais, Y.; Parra-Rapado, L. Tetrahedron Lett. 1996, 37, 1209
    • (1996) Tetrahedron Lett. , vol.37 , pp. 1209
    • Landais, Y.1    Parra-Rapado, L.2
  • 31
    • 0142182136 scopus 로고    scopus 로고
    • For an account concerning the ring-opening of cyclopropylcarbinols with mercury(II) salts, see
    • For an account concerning the ring-opening of cyclopropylcarbinols with mercury(II) salts, see: Meyer, C.; Blanchard, N.; Defosseux, M.; Cossy, J. Acc. Chem. Res. 2003, 36, 766
    • (2003) Acc. Chem. Res. , vol.36 , pp. 766
    • Meyer, C.1    Blanchard, N.2    Defosseux, M.3    Cossy, J.4
  • 32
    • 84855640403 scopus 로고    scopus 로고
    • See the Supporting Information for the preparation. No efforts were made to prepare single diastereomers since the product distribution from diastereomeric β-hydroxy sulfoxides was to be investigated
    • See the Supporting Information for the preparation. No efforts were made to prepare single diastereomers since the product distribution from diastereomeric β-hydroxy sulfoxides was to be investigated.
  • 44
    • 78651506230 scopus 로고    scopus 로고
    • The structure could not be assigned to cyclopropanes 46 and 47 at this stage. It could be assigned only based on the NOE analysis of the acetonide derived from 59
    • The structure could not be assigned to cyclopropanes 46 and 47 at this stage. It could be assigned only based on the NOE analysis of the acetonide derived from 59.
  • 45
    • 0041288450 scopus 로고
    • Mercuric oxide sequesters the liberated trifluoroacetic acid thus preventing the reaction mixture from becoming acidic. For the use of HgO see
    • Mercuric oxide sequesters the liberated trifluoroacetic acid thus preventing the reaction mixture from becoming acidic. For the use of HgO see: Giese, B.; Hueck, K. Tetrahedron Lett. 1980, 21, 1829
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1829
    • Giese, B.1    Hueck, K.2
  • 47
    • 78651511717 scopus 로고    scopus 로고
    • The inversion of sulfur configuration is expected based on precedented electrophile promoted nucleophilic sulfinyl group heterofunctionalization of alkenes, see ref 3
    • The inversion of sulfur configuration is expected based on precedented electrophile promoted nucleophilic sulfinyl group heterofunctionalization of alkenes, see ref 3.
  • 52
    • 37549059608 scopus 로고    scopus 로고
    • For the preparation of allylic alcohols by asymmetric vinylation of aldehydes see
    • For the preparation of allylic alcohols by asymmetric vinylation of aldehydes see: Salvi, L.; Jeon, S.-J.; Fisher, E. L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2007, 129, 16119
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 16119
    • Salvi, L.1    Jeon, S.-J.2    Fisher, E.L.3    Carroll, P.J.4    Walsh, P.J.5
  • 58
    • 0001485086 scopus 로고    scopus 로고
    • For the asymmetric synthesis of cyclopropanes see
    • For the asymmetric synthesis of cyclopropanes see: Li, A.-H.; Dai, L.-X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341
    • (1997) Chem. Rev. , vol.97 , pp. 2341
    • Li, A.-H.1    Dai, L.-X.2    Aggarwal, V.K.3
  • 65
    • 78651474519 scopus 로고    scopus 로고
    • The trans -cyclopropanes corresponding to 46 and 47 are expected to react without any incident to furnish anti -anti -syn and syn -anti -syn stereotetrads. Unlike cis -allylic alcohols 42 and 43 that could be separated, the corresponding trans -allylic alcohols, obtained by reduction of 41 with Red-Al, could not be separated. Therefore further sulfoxide preparation and cyclopropanation was not attempted
    • The trans -cyclopropanes corresponding to 46 and 47 are expected to react without any incident to furnish anti -anti -syn and syn -anti -syn stereotetrads. Unlike cis -allylic alcohols 42 and 43 that could be separated, the corresponding trans -allylic alcohols, obtained by reduction of 41 with Red-Al, could not be separated. Therefore further sulfoxide preparation and cyclopropanation was not attempted.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.